Fmoc-5-Hydroxy-L-tryptophan

Name: Fmoc-5-Hydroxy-L-tryptophan
Brand: ChemScene
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CAS No. 178119-94-3
Cat. No. CS-0149677
Purity≥95%
MDL No.MFCD28166517

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 178119-94-3

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General Information

CAS No. 178119-94-3
Cat. No. CS-0149677
Purity ≥95%
MDL No. MFCD28166517
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₂N₂O₅
Molecular Weight 442.46
Synonym(s) Fmoc-Trp(5-OH)-OH
SMILES OC=1C=CC2=C(C1)C(=CN2)C[C@@H](C(O)=O)NC(OCC3C4=CC=CC=C4C5=CC=CC=C53)=O

Description

Fmoc-5-Hydroxy-L-tryptophan integrates a photolabile Fmoc protecting group with a hydroxylated tryptophan side chain, enabling efficient solid-phase peptide synthesis. The electron-rich indole moiety supports selective derivatization, while the hydroxy group facilitates downstream functionalization in bioconjugation and peptidomimetic design.

Application

Fmoc-5-Hydroxy-L-tryptophan serves as a key building block for the synthesis of bioactive peptides and natural product analogs, enabling efficient solid-phase peptide coupling due to its orthogonal Fmoc protection. The 5-hydroxytryptophan side chain offers direct access to serotonin-related scaffolds and facilitates late-stage functionalization in medicinal chemistry campaigns. Its bench-stable, crystalline form simplifies handling and purification, while maintaining high compatibility with standard deprotection and coupling protocols.

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 111.65
LogP 4.4079
H_Acceptors 4
H_Donors 4
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Phenol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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Fmoc-5-Hydroxy-L-tryptophan

CAS No. 178119-94-3

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